Gold-Catalyzed Cyclization/Intermolecular Methylene Transfer Sequence of O-Propargylic Oximes Derived from Glyoxylates
Gold-Catalyzed Cyclization/Intermolecular Methylene Transfer Sequence of O-Propargylic Oximes Derived from Glyoxylates
复制标题
金催化乙醛酸衍生的 O-炔丙肟的环化/分子间亚甲基转移序列
DOI：
10.1055/s-0037-1611640
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发表时间：
2019
期刊：
影响因子：
--
通讯作者：
Itaru Nakamura
中科院分区：
文献类型：
--
作者：
Shinya Gima;Keigo Shiga;Masahiro Terada;Itaru Nakamura
我们通过C=N键断裂成功扩展了O-炔丙肟的金催化骨架重排反应，以包括肟部分上具有酯基的底物，以良好到高的产率提供在4位上具有烷氧基羰基亚甲基的相应2-异恶唑啉。我们的机理研究表明，烷氧基羰基亚甲基的转移以分子间方式进行，证实反应是通过环化进行的，然后是烷氧基羰基亚甲基的分子间转移。
We successfully extended our gold-catalyzed skeletal rearrangement reaction ofO-propargylic oximes through C=N bond cleavage to include substrates having an ester group on the oxime moiety, affording the corresponding 2-isoxazolines having an alkoxycarbonylmethylene group at the 4-position in good to high yields. Our mechanistic studies indicated that the transfer of the alkoxycarbonylmethylene group proceeded in an intermolecular manner, confirming that the reaction proceeds through cyclization followed by intermolecular transfer of the alkoxycarbonylmethylene group.